The Best Day Trips From Chicago, According To Locals

There are plenty of reasons to visit Chicago, Illinois, which has been called the best big city in America. It has tons of cultural destinations, ranging from live music venues to theaters. It has cool public art wherever you turn. It has delectable restaurants, including one with three Michelin stars that transcends expectations. It has natural beauty, including gorgeous gardens and lots of free beaches. However, if you don't venture outside the city limits a little bit, you're missing out on what this pocket of the U.S. has to offer. That's because within just two hours of Chicago are lots of great places to go for a day trip, ranging from a town that's been nicknamed the "Hamptons of Chicago" to one of the most biodiverse national parks in the country.

So, Islands rounded up the best day trips from Chicago based on who knows the area best — locals. To do so, we evaluated which spots within a two hour drive from the city are most often written about by local bloggers and journalists such as Midwest Living, OnMilwaukee, and more. Then, we considered which have the most unique activities for people of all interests, as well as the most activities, so you'll never have to head back to the Windy City earlier than you planned to. Drive times can vary based on traffic, but are accurate as of the time of writing.

With tons of theaters, museums, and music venues, Chicago is undoubtedly a cultural epicenter. However, visitors can explore more offbeat — and less crowded — cultural destinations in Bloomington-Normal. This lively college town has plenty of its own ways to experience culture, all just about a two hour drive from Chicago. One of its most prominent venues is the Theatre at Ewing, a distinctive, open air venue with 430 seats. If you're taking your day trip in the summer, then check out the Illinois Shakespeare Festival at this theater to truly take in its magic. If the silver screen is more your speed, then head to the historic Normal Theater instead. The restored 1937 Art Moderne theater showcases everything from classic to international films for film buffs looking for what's beyond their local AMC.

Bloomington-Normal has other nods to history, too. The town is home to the former residence of 1800s U.S. Supreme Court Justice David Davis, who was also an advisor and political consultant for Abraham Lincoln. The 1872 Victorian home is available for tours. Or, go on a self-guided tour of Cook Hall at Illinois State University, which was built in 1898 and is on the National Register of Historic Places. You can even make your day trip a weekend trip in historic digs at the Vrooman Mansion, a Romanesque-style bed and breakfast that dates back to 1869.

If you're on the hunt for a great souvenir from your Midwestern journey, you might just find it on your Cedarburg, Wisconsin day trip rather than in Chicago. After about a two hour drive from Chicago, you'll find tons of one-of-a-kind shops here, many on Washington Avenue, which Architectural Digest called one of the "Most Beautiful Main Streets in America." Just a few of the shops worth perusing on this historic street include Downtown Dough, a baking supply shop with more than 2,000 varieties of cookie cutters; The Gem Shop, the biggest gem and rock store in the region; and Birchwood Wells, which offers unique home goods and décor. Continue your shopping escapade in Cedarburg at the Cedar Creek Settlement, which houses more than two dozen shops in a refurbished mill that dates back to the 19th century.

Both the old and the new combine in the Cedar Creek Settlement and beyond in Cedarburg. A former haven for German and Irish immigrants, the town keeps its history alive by housing modern shops in charming old buildings. Some shops, restaurants, and attractions are inside nearly 200 year old stone structures. To learn more about Cedarburg's past, head to the Cedarburg History Museum, which showcases ever-changing exhibits. Or, enjoy the great outdoors while experiencing Cedarburg history at Covered Bridge Park, which has the state's last covered bridge that is also on the National Register of Historic Places.

Evanston is a city that's practically just like its big sibling of Chicago. But with its eight stunning beaches along Lake Michigan, wow-worthy mansions, and title of one of the coolest suburbs in America by Apartment Therapy, it feels like a world away. Plus, it's just a 30- to 45-minute drive from Chicago. Day trippers especially love Lee Street Beach, Greenwood Street Beach, and Clark Street Beach. The Evanston shores also house the Grosse Point Lighthouse, which dates back to the 1870s and is on the National Register of Historic Places, as well as three historic shipwrecks.

Back onshore, Evanston has a dining scene worth drooling over. The city has many restaurants featuring tons of cuisines, making it clear why Evanston was called one of the best suburbs in America for foodies by Thrillist. Just a few of the favorite eateries include Tapas Barcelona, a trendy and bustling spot for Spanish inspired tapas, and Five & Dime, a rooftop yet casual bar and restaurant. Like any good food town, Evanston also has a great farmers' market. Its Downtown Evanston Farmer's Market features more than 60 vendors from May to November. You can top off your meal at many of the breweries and distilleries that call Evanston home as well. With so much to clamor over in Evanston, it's no surprise that tons of television shows and movies were set here, including "Cheaper by the Dozen," "Dennis the Menace," "Sixteen Candles," "Uncle Buck," and more.

Chicago is a bustling city full of skyscrapers, cars, and crowds. But after visitors have their fill of the concrete jungle, they can escape to one of the most biodiverse national parks in the country that's just about an hour's drive from Chicago. Indiana Dunes National Park in Porter, Indiana, offers a huge variety of terrain, which can all be explored via 50 miles of trails through 15,000 acres. Some of the best trails include the diverse, 5-mile Cowles Bog Trail, as well as the 3-mile Heron Rookery Trail, which is one of the top spots to see the park's famous wildflowers.

Throughout these trails, visitors can spot more than 350 types of birds — which makes Indiana Dunes one of the national parks with the most bird species — and more than 1,100 types of flowering plants and ferns. The park also protects over 1,000 acres of the last oak savannas on the planet. But as its name suggests, the dunes are Indiana Dunes National Park's most famous asset. Its most notable dune is the 126-foot Mount Baldy, which moves a dozen feet every year. Even history fans will find something to revel in at the park, since it also has Honore Gratien Joseph Bailly de Messein's unique 19th-century former home, a National Historic Landmark. Bailly de Messein, a French Canadian fur trader, helped to develop the area.

If a hearty hike or bike ride to breathe in the fresh, Midwestern air is what you're after, then set your sights on Janesville, Wisconsin. Dubbed the City of Parks, Janesville is about a two hour's drive from the city and has more than 2,000 acres of trails. It also has more than 50 parks to explore, plus several other ways to experience the outdoors. Janesville is home to the Rotary Botanical Gardens, which has been named as one of the best plant gardens in America and one of the best Japanese gardens on the continent. Throughout its 20 acres, you can see more than 4,000 types of plants as well as hummingbirds, dragonflies, and butterflies. More than 150,000 people visit the gardens every year.

Janesville treasures its history as much as it treasures its natural resources. Twenty percent of all of the state's National Register of Historic Places buildings are in Janesville. Perhaps Janesville's most famous historic building is the Lincoln-Tallman House, a home formerly owned by William Morrison Tallman, that was visited by Abraham Lincoln. More than three quarters of the upscale home's furnishings are original, making the house a great way for visitors to see how the other half lived during the late 19^th century. The Italianate house can be visited on hour-long tours that cost $20 per person.

If you want to appreciate the majestic Lake Michigan shoreline while still enjoying access to city delights like shops, restaurants, and museums, look no further than Kenosha, Wisconsin, which is about an hour and a half drive from Chicago. Most of the lake's shoreline is available to the public, and you might even see the Chicago skyline from it, depending on the weather. To see migrating birds and other beach wildlife, check out the Chiwaukee Prairie near the shore. The Kenosha shore is also home to two lighthouses, including the Southport Light Station, which was built in 1866, and the North Pier Lighthouse, which was built in 1906.

Kenosha also has robust access to its history through its five museums. Those include the Civil War Museum, which offers information about the Civil War from the distinct perspective of Midwestern people by sharing personal anecdotes and objects; the Dinosaur Discovery Museum, which shows how birds evolved from dinosaurs through guided tours; and the Kenosha Public Museum, a natural sciences and fine and decorative arts museum with over 80,000 works. To learn about Kenosha's own history, check out the Kenosha History Center. However, you don't have to stay indoors to explore Kenosha's history. The city is home to four historic districts — Library Park, Third Avenue, Civic Center, and Pearl Street — all which have guides and walking tours.

Getting to the Hamptons from New York City is a notorious pain, but you won't need to sit in traffic to experience the "Hamptons of Chicago." Lake Geneva, Wisconsin is about two hours from The Windy City and features water views, a chic flair, and jaw-dropping mansions. You can get a front-row seat to those mansions thanks to the more than 20-mile public walking path — a rarity among American lakes — that encircles the more than 5,000 acre lake. If you don't feel like walking, the Lake Geneva Cruise Line also offers sightseeing from the water. From both the path and cruise, you'll see the Yerkes Observatory, one of America's most important ground-based observatories that's housed in a historic building, as well as Blacktoft, an 1881 mansion that was the residence of a women's suffrage movement activist.

If gazing at the lake's spring-fed, crystal-clear waters makes you eager to jump in, don't worry, you can. Visitors can rent kayaks, paddleboards, and motorboats, and also swim and fish in the lake. With so much to do in Lake Geneva, it's easy to be swayed into making your day trip here a weekend trip. If you do, you can stay in style, as the town has several impressive lakefront hotels. The AAA Four-Diamond Grand Geneva Resort & Spa has tons of amenities over its 1,300 acres, as well as history, since it was a former Playboy Club.

Chicago is the biggest city in Illinois, but a little over an hour and a half drive away is Milwaukee, which is the biggest city in Wisconsin. Known as the Brew City, Milwaukee has over 50 breweries, including Miller Brewing Company. To try beers from several breweries in one shot, head to Milwaukee's best bars overlooking the water for good vibes and better beers. Visitors can also tour where Pabst beers were once brewed and tour the Gilded Age's Pabst Mansion, which was owned by the Pabst family. True hopheads won't be able to resist staying overnight in Milwaukee, as there are even hotel rooms inside the original Pabst Blue Ribbon brewery.

There are also plenty of award-winning restaurants to chase down your beer with. Eighteen James Beard Award-recognized chefs and restaurants are in the area, like 1033 Omakase, a Japanese eatery that presents course after course of chef-curated sushi dishes; and Solly's Grille, a 1936 throwback spot known for its Wisconsin butter burgers. You can also taste a little bit of everything at the Milwaukee Public Market, which, with almost 20 local vendors, has been called one of the best public markets in the country by Frommer's. All of those delicious eats make for an excellent precursor to the many theater productions showcased in town. The Milwaukee Theater District, which is home to more than a dozen live arts organizations, has the highest number of theater seats per capita in the country.

There are lots of shorelines to check out around Lake Michigan, but few have a harbor quite as massive as New Buffalo's, despite its small town vibe. Just an hour and a half drive from Chicago, the Michigan town has one of the biggest recreational harbors in the area, and it's packed with things to do for day trippers. That even includes solo travelers, as New Buffalo is one of the five adorable towns near Chicago that are perfect for solo trips. Visitors can spread out on New Buffalo Beach, which has nearly 800 feet of sand, or get in the water and fish, cruise, paddle, sail, or swim. You also might be able to see Chicago from here.

No worries if you're not a beach rat, either. You can still enjoy Mother Nature in New Buffalo as there are over 13 preserves and natural areas in town. You'll even find spots for the whole family, such as New Buffalo Memorial Township Park, which has a playground and splash pad, and Galien River County Park, which has hiking and biking trails. With such a picture perfect resort town vibe, it's no surprise that Southwest Michigan, which is home to New Buffalo, has been named as one of the 50 Best Places to Travel in 2022 by Travel + Leisure.

Although Chicago does have some family-friendly fun, it's more of a playground for adults. However, just a less than two-hour drive from Chicago, families can find something for those of every age in Rockford, Illinois. It's also known as the "City of Gardens" due to its stunning green spaces, outdoor thrills, and endless recreation. 

One spot in town that's guaranteed to get kids' jaws on the floor is the Burpee Museum of Natural History, which is home to a juvenile Tyrannosaurus rex skeleton with more bones than any other on display on earth, as well as plant and dinosaur fossils. Kids can continue to learn and have fun at the Discovery Center Museum, an interactive museum with more than 300 exhibits. Or, take the fun outdoors at the 155-acre Klehm Arboretum and Botanic Garden, which has a butterfly garden, labyrinth, a playground, a stumpery, and a sundial.

Rockford is also a haven for architecture buffs. The town is home to the Laurent House, which Frank Lloyd Wright designed for Navy veteran Kenneth Laurent. The only home that Wright designed for a person in a wheelchair, the Laurent House features an indoor-outdoor connection as well as 3-foot-wide doors and halls.

St. Charles, Illinois may not have the access to Lake Michigan that some of the other towns on this list enjoy, but it does offer its own unique water respite, making it one of the best Chicago suburbs to visit. The town, which is an hour and a half drive from Chicago, is on the Fox River, and there are plenty of opportunities to experience it firsthand on a river boat cruise or kayak or paddle boat. 

If you would rather stay on land, there's even more to gaze at. St. Charles has more than 180 pieces of public art lining its streets, ranging from murals to statues. As you meander the town checking out the art as you find it or on a self-guided tour, make a point to stop at some of the many breweries in St. Charles. Just a few of the breweries you can choose from include Pollyanna Brewing Co., which has views of the Fox River, and Riverlands Brewing Co., which has a beer for practically every palate.

If you're ready to trade your view of skyscrapers for views of canyons and waterfalls, then take about a two hour drive from Chicago to Starved Rock State Park in Oglesby, Illinois. This park has 18 sandstone canyons — all distinct from one another — that were formed by melting glaciers more than 14,000 years ago. "Starved Rock completely exceeded every expectation I had," wrote one past visitor on Google. "I've traveled quite a bit and honestly didn't expect to find scenery this breathtaking just a couple of hours from Chicago. The entire experience felt almost cinematic."

To see the canyons spread across more than 2,600 acres along the Illinois River, hop on more than a dozen miles of trails for a hike. Some of the favorite trails include the 4-mile LaSalle Canyon Trail, which takes visitors to LaSalle Canyon and its waterfall, as well as the 2.6 mile Starved Rock and Sandstone Point Overlook, which offers all-encompassing river views. People can also camp, fish (with a license), or boat in certain areas of the park. Best of all, admission and parking at this park is free. After you've had your fill here, check out Matthiessen State Park, which is Starved Rock State Park's under appreciated neighbor that's a surreal Illinois gem full of canyons and waterfalls.